1. Field of the Invention
This invention relates to the use of certain N-heterocyclic ring-substituted phenylacetonitrile derivatives as herbicides which are effective against a variety of weeds, particularly barnyardgrass (Echinochloa crus-galli), as post-emergence and especially pre-emergence growth inhibitors in rice fields for transplanted rice under aquatic, or flood, conditions as occurs in rice paddys.
2. Description of the Prior Art
Buchel et al., U.S. Pat. No. 3,732,242, issued May 8, 1973, discloses phenylimidazolyl-fatty acid derivatives having the formula: ##STR2## wherein: R.sup.1, R.sup.2 and R.sup.3 are the same or different and are hydrogen or lower alkyl;
R.sup.4 is hydrogen, alkyl, lower alkoxy, lower alkyl mercapto, or an electronegative moiety; PA1 R.sup.5 is benzene, benzene substituted by alkyl, lower alkoxy, lower alkylmercapto or an electronegative moiety, or R.sup.5 is an aliphatic moiety; PA1 X is a carboxyl moiety or a grouping of a functional carboxylic acid derivative; PA1 m is 0, 1, 2, 3, 4, 5, or 6; and PA1 n is 0, 1 or 2, PA1 R.sup.2 is a halogen atom, preferably a chlorine or bromine atom, an alkyl group, preferably having 1 to 4 carbon atoms, an alkoxy group, preferably having 1 to 4 carbon atoms, a trifluoromethyl group, or a nitro group, PA1 R.sup.3 is a hydrogen atom or an alkyl group, preferably having 1 to 4 carbon atoms, most preferably a methyl group, PA1 R.sup.4 is a hydrogen atom or an alkyl group, preferably having 1 to 4 carbon atoms, most preferably a methyl group, PA1 n is 0, 1, or 2, and PA1 m is 0, 1, or 2 PA1 R is selected from C.sub.6 H.sub.5, C.sub.6 H.sub.4 --X wherein X is as defined above, straight or branched chain (C.sub.1 -C.sub.8) alkyl, (C.sub.3 -C.sub.6) saturated or unsaturated cycloaliphatic groups, C.sub.6 H.sub.5 CH.sub.2 or C.sub.6 H.sub.5 S; PA1 n is selected from 0, 1 or 2; PA1 m is selected from 0, 1 or 2; PA1 A is selected from CN and C.dbd.CH; and PA1 Z is a N-heterocyclic group selected from: ##STR7## or an agronomically-acceptable acid addition salt thereof. PA1 X is selected from hydrogen, (C.sub.1 -C.sub.4) alkyl, F, Cl or Br; PA1 R is selected from C.sub.6 H.sub.5 or C.sub.6 H.sub.4 --X wherein X is H, (C.sub.1 -C.sub.4) alkyl, F, Cl or Br; PA1 n is 0; and PA1 Z is selected from: ##STR8## PA1 X is selected from hydrogen, (C.sub.1 -C.sub.4) alkyl, F, Cl, Br, NO.sub.2 or SO.sub.2 C.sub.c H.sub.5 ; PA1 R is selected from C.sub.6 H.sub.5, C.sub.6 H.sub.4 --X wherein X is as defined above, straight or branched chain (C.sub.1 -C.sub.8) alkyl, (C.sub.3 -C.sub.6) saturated or unsaturated cycloaliphatic groups, C.sub.6 H.sub.5 CH.sub.2 or C.sub.6 H.sub.5 S; PA1 n is selected from 0, 1 or 2; PA1 m is selected from 0, 1 or 2; and PA1 Z is a triazolyl group having the empirical formula C.sub.2 H.sub.2 N.sub.3.
and pharmaceutically acceptable non-toxic salts thereof, and processes for the production of such compounds of the formula shown above. These compounds are particularly useful for their antimycotic activity and are intended to be administered to humans and animals.
A preferred group of compounds disclosed in this patent and represented by the formula (I) in the foregoing paragraph is that wherein X is a carboxyl group of the formula --COOR.sup.6 wherein R.sup.6 is straight or branched chain alkyl of 1 to 10 carbon atoms or benzyl or an amide group of the formula: ##STR3## wherein R.sup.7 and R.sup.8 are the same or different, and are hydrogen or methyl, or R.sup.7 and R.sup.8 together with the amide nitrogen form a morphilino or piperidino ring. The salts may be formed with any of the known physiologically compatible acids such as hydrohalic acids, phosphorous acids, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids.
Example 9 of this patent discloses the preparation of the specific compound, diphenyl-imidazolyl-acetonitrile, having the formula: ##STR4##
Buchel et al., U.S. Pat. No. 3,826,836 issued July 30, 1974, which is a division of the aforementioned U.S. Pat. No. 3,732,242, contains claims drawn to the pharmaceutical composition and the method of combatting mycotic infections disclosed in the earlier U.S. Pat. No. 3,732,242.
Buchel et al., U.S. Pat. No. 3,842,078 issued Oct. 15, 1974, which is also a division of U.S. Pat. No. 3,732,242, contains claims drawn to diphenyl-imidazolyl-acetic acid morpholide or the hydrochloride salt thereof.
Buchel et al., U.S. Pat. No. 3,978,069 issued Aug. 31, 1976, which is also a division of U.S. Pat. No. 3,732,242, contains claims drawn to diphenyl-imidazolyl-acetic acid piperidine or the pharmaceutically acceptable salts thereof.
Buchel et al., U.S. Pat. No. 4,018,924 issued Apr. 19, 1977, which is a continuation-in-part of U.S. Pat. No. 3,732,242, contains claims drawn to diphenyl-imidazolyl-acetic acid piperazide, pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof.
Yih and Yu, U.S. Pat. No. 4,009,021 issued Feb. 22, 1977, assigned to the same assignee to which the present application is assigned, discloses as plant growth regulating agents compounds having the formula: ##STR5## wherein: R.sup.1 is a halogen atom, preferably a chlorine or bromine atom, an alkyl group, preferably having 1 to 4 carbon atoms, an alkoxy group, preferably having 1 to 4 carbon atoms, a trifluoromethyl group, or a nitro group,
and the agronomically-acceptable acid addition salts thereof. The imidazole acid addition salts include salts of the compound of formula III above with hydrochloric acid, hydrobromic acid, hydrofluoric acid, nitric acid, perchloric acid, sulfuric acid, phosphoric acid, chloracetic acid, oxalic acid, formic acid, acetic acid, maleic acid, succinic acid, benzenesulfonic acid, p-toluenesulfonic acid, tartaric acid, lactic acid, and the like.
Miller, Chan and Carley, U.S. Pat. Nos. 4,073,921 and 4,143,137, the latter being a division of the former, both being assigned to the same assignee to which the present application is assigned, disclose substituted arylcyanoalkyl and diarylcyanoalkyl imidazoles, their acid addition salts and their metal salt complexes and their use as broad spectrum protectant-eradicant fungicides.
Sury and Hoffman, Helv. Chim. Acta., 37, 2133 (1954), disclose diphenyl-4-pyridylacetonitriles as intermediates for producing central nervous system stimulating agents.
British Pat. No. 1,361,816 and the corresponding Netherlands Pat. No. 7,117,312, disclose diphenyl-2-pyrazylacetonitriles having herbicidal and plant growth regulatory activity.
U.S. Pat. Nos. 3,868,244 and 3,887,708 and the corresponding French Pat. No. 1,569,940, disclose the preparation and fungicidal activity of diphenyl-5-pyrimidylacetonitriles.
U.S. Pat. No. 3,655,359 discloses diphenyl-3-pyridylacetonitriels having herbicidal activity.